N-(substituted phenyl) pyrazolo arketone derivatives, preparation method and application thereof

A technology of pyrazoloalkone and its derivatives, which is applied in the field of organic chemistry, can solve the problems of synthesis of alkone derivatives, few reports on insecticidal activity, poor contact activity, etc., and achieve simple and feasible synthetic route and good antibacterial activity , good growth inhibitory and poisonous activity

Inactive Publication Date: 2018-07-10
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, arketone also has strong stomach poisoning activity against test insects, but relatively poor contact activity ( M, et al. 2010. Pestic Biochem Physiol, 98:263)
[0006] However, there are few reports on the synthesis and insecticidal activity of alkone derivatives, mainly from the synthesis of a series of alkone hydrazone / ester derivatives in the early stage of this project, and it was found that some compounds have good growth and development against the third instar armyworm Inhibition and toxicity (Guo Y, et al.2012.J.Agric Food Chem.,60:7016; Guo Y, et al.2012.BioorgMed Chem Lett,22:5384; Guo Y, et al.2013,J .Agric Food Chem.,2013,61,11937)

Method used

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  • N-(substituted phenyl) pyrazolo arketone derivatives, preparation method and application thereof
  • N-(substituted phenyl) pyrazolo arketone derivatives, preparation method and application thereof
  • N-(substituted phenyl) pyrazolo arketone derivatives, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 Synthesis of 4-carbonyl-5-(dimethylaminomethylene) alkone (c)

[0028]Dissolve 200mg of chromium trioxide and 316.4mg of pyridine with anhydrous dichloromethane, then add 1.8g of tert-butyl hydroperoxide and stir for 3 minutes, finally add 464mg of alkone, react at room temperature, TLC detection, the reaction is complete Afterwards, the compound alkone ketone was separated by column chromatography under reduced pressure; 246 mg of the compound alkone ketone was dissolved in an appropriate amount of toluene, and then 143 mg of N,N-dimethylformamide dimethyl acetal was added at 110 ° C. The reaction was detected by TLC. After the reaction was complete, it was concentrated under reduced pressure and separated by column chromatography to obtain 4-carbonyl-5-(dimethylaminomethylene) alkone (c).

[0029] The physical and chemical properties of 4-carbonyl-5-(dimethylaminomethylene) arketone (c):

[0030] 1), orange-yellow solid, melting point 66-68°C.

[0031] 2),...

Embodiment 2

[0035] Example 2 N-phenylpyrazolo alkone derivatives (compound 1)

[0036] Dissolve 72.3 mg of 4-carbonyl-5-(dimethylaminomethylene) arketone (c) and 31.1 mg of phenylhydrazine hydrochloride in absolute ethanol, heat to reflux, and track and detect with TLC. After the reaction is completed, depressurize After concentrating and spinning the ethanol to dryness, adding an appropriate amount of dichloromethane to dissolve, and then separating by thin-layer chromatography to obtain pure compound 1 with a yield of 83%.

[0037] The physical and chemical properties of compound 1 are as follows:

[0038] 1), orange-yellow solid, melting point 85-88°C.

[0039] 2), the infrared spectrogram (IR) feature of this compound:

[0040] Using potassium bromide tablet method: 2961, 2923cm -1 Stretching vibration absorption for saturated hydrocarbons, 1736cm -1 Stretching vibration absorption for lactone carbonyl, 1024cm -1 It is C-O-C stretching vibration absorption.

[0041] 3), the nucl...

Embodiment 3

[0043] Example 3 N-(2-fluoro-phenyl) pyrazolo arketone derivatives (compound 2)

[0044] Adopt the method described in embodiment 2 to synthesize compound 2, the physicochemical property of compound 2 is as follows:

[0045] 1) Light yellow solid, melting point 204-206°C.

[0046] 2), the infrared spectrogram (IR) feature of this compound:

[0047] Using potassium bromide tablet method: 3132cm -1 Stretching vibration absorption for unsaturated hydrocarbons, 2962, 2925cm -1 Stretching vibration absorption for saturated hydrocarbons, 1741cm -1 Stretching vibration absorption for lactone carbonyl, 1041cm -1 It is C-O-C stretching vibration absorption.

[0048] 3), the nuclear magnetic resonance spectrum of this compound ( 1 H NMR, 400MHz) features:

[0049] With deuterated chloroform as the solvent and TMS as the internal standard, the peaks are assigned as follows: δ: 7.60-7.67 (m, 2H, -Ph and-CH=N-), 7.53 (s, 1H, H-2′), 7.45-7.52(m,2H,-Ph andH-5′),7.31-7.35(m,1H,-Ph),7....

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Abstract

The invention belongs to the field of organic chemistry, and discloses a series of new N-(substituted benzene)-based pyrazolyl ketone derivatives, and a preparation method and application thereof. The series of compounds are prepared through the steps of taking fraxinellone as a raw material, carrying out a series of reactions to obtain fraxinellone ketone, then reacting the fraxinellone ketone with different substituted phenylhydrazine hydrochloride to obtain the series of N-(substituted benzene)-based pyrazolyl ketone derivatives, and the structural general formula of the N-(substituted benzene)-based pyrazolyl ketone derivatives is shown in the description. The compounds disclosed by the invention have very strong growth inhibition and poisonous activity against three-year-old armyworms, part of the compounds are better than parent fraxinellone and positive control toosendanin, and are expected to be used to prepare new-style natural product insecticides, in addition, the compounds disclosed by the invention exhibit better bacteriostatic activity against some bacteria, and are expected to be developed into potential natural product bacteriostats.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and relates to alkone derivatives, in particular to a series of N-(substituted phenyl) pyrazolo alkone derivatives with insecticidal and bacteriostatic activities and a preparation method thereof and the series of derivatives in Applications in the preparation of natural product insecticides and bacteriostats. Background technique [0002] [0003] Fraxinellone is a natural degraded limonoid compound with an α-substituted furan ring structure. In 1965, Pailer et al. initially determined its structure, and then in 1969, Coggon et al. isolated alkone from D.albus.L. for the first time, and proved its absolute configuration by X single crystal diffraction for the first time (Coggon P, et al. 1969. J Chem Soc D, Chem Commun, 828). At present, arketone can be extracted and isolated from many Rutaceae plants or Meliaceae plants, such as: D. angustifolius, Fagaropsis glabra, Raulinoa echinata, Fre...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/048A01N43/90A01P1/00A01P7/04
CPCA01N43/90C07D491/048
Inventor 郭勇曲来亮王晓光钟雪杭婷
Owner ZHENGZHOU UNIV
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